The Daily Stoic - Molly Bloom on Turning Down 5 Million Dollars

Episode Date: January 21, 2023

Ryan speaks with Molly Bloom about her book Molly's Game: The True Story of the 26-Year-Old Woman Behind the Most Exclusive, High-Stakes Underground Poker Game in the World, the crossroads moment that taught her to overcome challenges through mindfulness, the intoxicating and eye-opening effects of running poker games for the ultra-rich and famous, how hitting rock-bottom taught her that good character is something to be trained, and more.Molly Bloom is an entrepreneur, author, speaker, and former Olympic class skier. After her competitive skiing career was derailed by injury, Molly became a bartender at the Viper Room in Los Angeles. She eventually started an event and catering company to host high-stakes poker tournaments, which attracted wealthy people, sports figures, and Hollywood celebrities. In 2013, she was sentenced as part of a $100 million money laundering and illegal sports gambling operation and served one year of probation with a $200,000 fine, and 200 hours of community service. Her story was turned into a 2017 film written and directed by Aaron Sorkin. Molly’s speaking and entrepreneurial work focuses on inspiring and educating people on how to become top performers.✉️  Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.📱 Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hey, prime members, you can listen to the Daily Stoke podcast early and add free on Amazon music. Download the app today. Welcome to the weekend edition of the Daily Stoke. Each weekday we bring you a meditation inspired by the ancient Stokes. Something to help you live up to those four Stoke virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview stoic philosophers. We explore at length how these stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space when things have slowed down,

be sure to take some time to think, to go for a walk, to sit with your journal, and most importantly to prepare for what the week ahead may bring. Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic podcast. I am here. Well, I'm not at the Painted Porch. I'm down in Florida with the family. And I just finished today's guest wonderful, fascinating book. I've known Molly Bloom for a while.

We connected on Instagram. We're actually supposed to do this at the painted porch in person not too long ago. We bought a bunch of her books, she was going to sign them and then they also rolled out at the bookstore and she couldn't come because she was expecting her first kid. So that's why I was late finishing the book but Molly's game, the true story of the 26 year old woman behind the most exclusive high stakes underground poker game in the world, also fascinating and wonderful Aaron Sorkin movie, which I highly recommend.

This might not seem like it has much to do with Stoicism, but actually we go way in depth into integrity, into being drawn towards the wrong path and how to get back on it, how to find the rhythm, your character, your character, your character virtue, as Mark's Relious writes about in meditations. We talk about risk, we talk about finding mirror life's task, we talk about a whole bunch of fascinating stuff. There's a really awesome conversation and we we're gonna do it again in person because I had so much fun.

And I think this was such a good conversation. I think even more will come out of it in person. Molly is an American entrepreneur, a speaker and an author of this bestselling book Molly's Game. But before that she actually trained to be an Olympic skier. Her brother was a multi-gold metal winner. She almost qualified for the Olympics, but suffered a devastating career ending injury. And like Zeno, this changes the course of her life,

although not immediately for the better. She ends up running a high-stakes poker game. The Viper Room in LA was some of the richest, most famous, most influential people in the world. But it leads her astray. She gets hooked on drugs. She starts breaking the law. In fact, originally it wasn't illegal. She gets a little greedy. But it's a fascinating trajectory, a brilliant memoir.

I really enjoyed it. And then towards the end, it comes to a moment of truth, crossroads-esque moment where she has to decide what kind of person she's going to be, what is she actually value, who does she want to be. And that's where we end up in the discussion. You can follow her on Instagram and Twitter at I'm Molly Bloom and do read the book Molly's game and watch the movie. I think you'll really like both of them. I think you're really gonna like this conversation. Look forward to the follow up episode in person,

very, very soon as well. Hi, I'm David Brown, the host of Wendery's podcast business wars. And in our new season, Walmart must fight off target, the new discounter that's both savvy and fashion forward. Listen to business wars on Amazon music or wherever you get your podcasts. We're supposed to do this in person, but you had a pretty good

excuse. Yeah, yeah, the child. How's that going? It's going in, you know, really well, it's, it's certainly been a journey. She's 10 months now. We're starting to get to the place where it's not in the trenches so much, you know, different trenches. Different trenches. Yeah, different. They're gonna like that rock climbing while I think. It's here. Yeah, already is, then I get it.

She comes in here and she's like, woo! That's amazing. Well, I'm very excited to do this. I am too. I've been looking forward to this for a while and wanting to do it. I couldn't be more aligned with the things that you care about and your books have then extraordinarily important in my life. So this is really cool.

Well, that's an honor to hear. It's funny. I was, I, I think almost every review that I, I read of the movie, talked about Jessica Chastain's stoicism, like using it in the lower case sense, but like multiple reviews that I read all commented on that aspect of her personality. And so I was curious because we've never met how much of that you found rang true in you or was that what you aspire to be? Well, it's interesting because I think I started out life Incredibly sensitive and emotional and and then sort of formulated through

Through sports through the type of father I was raised by, through watching poker and understanding the value of game theory and other, other rational, then I was a philosophy minor in school. So I developed, um, stoicism to survive myself and to, because I saw that it was, you know, both important for success in the world, but also for surviving your life. Yeah. When you're kind of wired that way. Yeah, it must be interesting as an athlete.

You have to be super passionate about what you do and you have to be sort of deeply emotionally invested in what you're doing. And yet at the same time, figure out a way to strip emotion out of what you're doing as you're doing it because I'm rarely make good decisions out of emotion. No question. So it's like be all in on training, be all in on, on, you know, being as committed as you can and then learn how to surrender and detach. Yeah. And you have to feel the outcomes very intensely, but then also immediately move on from them and wipe the slate clean victory or defeat.

And it's mostly defeat, right? Especially, I mean, especially when you are ascending, like, sure. Anytime you, you're aspiring to do something, you start out at the bottom and you suck forever. No, and then you don't one day, hopefully, but. Yeah, there's a great quote from Ira Glasser, who's talking to someone who wanted to be in radio or something, and he said, when you're starting out, there's a gap between talent and taste. So like you have, you're early on your taste, or I guess in sports, it'd be like your

standards for like what is good or not good, is almost always gonna be much higher than you're physically capable of achieving, especially on at least in any consistent basis. So you have to be able to be comfortable with that that like it feels like what you're doing is shit compared to your heroes, but that's because they're way way better than you.

And yet you can't let that discourage you or you'll never actually get to where they are. Right. Yeah. And I think that that's where most people, because you have to stay in that suckiness and that sort of like it feels so far away and just the effort without return phase for so long. And I think that's where most people give up. Yeah, I'm going through that right now because I'm doing this series of four books in four years.

So like usually like when you do a big project, there's like the beginning part, it's insane. I don't know what I was thinking. Insane. They're, you know, like usually you start out of the thing and then there's the curve and it gets better and better and better and better and then it gets to whatever the final product is, which is never perfect, but you're proud of it. Then there's usually a big gap, sorry about gaps, there's a gap between starting the next one.

But on these projects, the gap between finished, after I finished the first book, and then was at page zero of the second one, was only a few months. So it was disorienting and really discouraging because you were like three months ago, you were editing almost, I don't wanna say perfect, but almost publishable prose. And then three months later, you're in, as Hemingway said, the first draft of everything is shit.

You're deep in the shit of it. And if you can't, if you feel that, if you're like, this is shit, so I'm shit, I quit, right? You won't get where you want to go. I have to imagine, because you came back from a number of injuries too. That must be that hard for an athlete in that sense, where you're like, I was so good at this, I could do this in my sleep, and now I suck.

For sure. I mean, I, you know, I was, my brothers and I were competing in mobile skiing. I was winning all the time. I was, you know, 10, 11 years old. Everyone was super excited about the future. And then I got diagnosed with really severe scoliosis. My spine was curved at like a 63 degree curve. And they had to essentially fuse my top 11 vertebrae together.

Well, first they had to try to straighten my spine. Fused the vertebrae together, put two metal rods on the side and so getting back on the mountain, which was, my doctors said no, everyone said no. But I just knew I had to try it. But yeah, to try to learn how to use your body again. And especially at 12 years old when everyone's telling you, this is not gonna be possible.

Sure. To feel also that your body's not responding in that way, but then to just have this, sort of, yeah, it was so in me, the fire was so in me that I just, I had to do it. And that was such a profound lesson in my life that, you know, the odds can be sacked against you. The experts can be telling you that it's not possible. Your own body and mind can be telling you that it's not possible.

But if you can tap into that sort of fury, it can overcome all that stuff. It's a, you know, it's a tough way to go. That must have been the grand like that, but. I must have been weird because I remember being checked for scoliosis, like they would line us all up in school and they would check you, but nobody ever had it, but you apparently actually got it. And I would always get checked in those things, and like, you look great, you know, and these aren't qualified medical professionals. It's your second grade math teacher. Exactly. So yeah, so that was a trip, you know, but, but I think that that informed me and, and, you know, taught me from a young age that life is more malleable than they, than they

tell you it is, you know. But it's not, it's not infinitely malleable, right? Because at some point that road for you as a skier ends, right? And that must be so hard, especially for athletes. But I think for any, it's like, you got where you were by defying the odds, by not listening to pronouncements, by rejecting the certainty that this or that was impossible or over or whatever. But you're on borrowed time. Like it doesn't last forever. Eventually that becomes like eventually they're right, right? And so knowing when to listen and not to listen is everything. Yeah. Yeah. And so was it like if you have been the person who was like fuck you you're wrong

Your whole life and then and then how do you come to terms with with the dream ending? That was a another Incredibly difficult, but then the lesson that came from it, I've used my whole life. And so I was at the University of Colorado. I made it all the way to, I made it to the USG team. I was third overall in North America. And I made it to Nationals that year, which was an Olympic qualifying event. And then I fell and just knew that I didn't have four more years in me.

And I went back to school, I had just taken the LSATs. And I say this all the time because in the movie, like my LSAT score was like perfect, but that's not what it was in real life. Like Sorkin inflated my LSATs score. But I.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S.S. I didn't know who I was. I would stay up all night just trying to, what if I had chosen a different line? Like, you know, I couldn't get passed it. And so finally I called my dad and my dad's a psychologist.

Another thing I always say is growing up with a psychologist for a father when you're a teenager is like the worst thing ever But it's kind of it can be really great as as an adult because You have this therapist on call and and he said Look You know This is this is a sort of watershed moment for you You have to start to be able to establish some agency over what's

going on in your head. Because I was so stuck in this loop and I couldn't separate myself from just this feeling that life was over. And so he and I had lots of talks about, and this was, I guess, my first introduction to mindfulness is being able to observe the thoughts, observe what's going on in your head and rise above it or move your focus to something else or surrender that. And instead of just getting caught into that loop over and over and letting it just destroy you. And so he taught me to be to kind of train in that. He was like, it's just like training and skiing

where you're gonna observe these thoughts, these negative thoughts are gonna come into your mind. And you know, on your good days, you're gonna be able to just detach from it on your bad days. Sometimes you gotta go to war with that voice. You know, sometimes you gotta get inside and be like, fuck this, eff this, you know. I going to, I'm not going to, I'm 21 years old.

This is not the end of my life. And he really taught me how to start kind of establishes some agency over that later down the line. I had to learn it in a much more significant way. But so I learned how to overcome it through mindfulness and through sometimes going about it. What's, it's acceptance, right? It comes down to a certain point, you have to face facts, you have to accept things. You can't always know a amount of willpower

can defy. It's interesting, because the Stokes code, there's stuff that's in our control and the stuff that's out of our control, which is true. And we're really bad at making that distinction, but the reality is there's also stuff that's kind of in the gray area in the middle.

And those are the things that you can kind of say, fuck you too. There's the stuff that's on the far end of the spectrum that looks at like it's outside your control, but actually it's 1% in your control, and if you're super talented and skilled and lucky in all these other things, you can flip what other people think is impossible.

But it's sort of knowing the limits of that ability to influence that then puts you face to face with the stuff that you have to accept. Like, hey, this is the end of the road for me in this thing. This is what my body can handle or can't handle. This is what my heart's not in it. Or just like in poker, you gotta know when to fold them. Absolutely.

That's right. Well, you know, I talked to Annie Duke recently and she was talking about this is like, we think about like quitting, she was saying, this sort of all or nothing thing. When in fact, it's kind of like, I don't think she said this when I'm making that, but it's kind of like a Russian nesting doll.

There's like, you know, there's quitting the hand, there's quitting the game that you're in, and then there's quitting playing all together, you know, there's quitting the hand, there's quitting the game that you're in, and then there's quitting playing altogether, like, period. Right? So it's like just because you're, just because you're facing facts, you're resigning in one aspect, doesn't mean you have resigned yourself completely. Do you know what I mean?

I think, understanding that accepting something doesn't mean you become instantly passive and giving up all agency over your life. You've just come to the end of one specific road. Yeah, and I think being able to have that ability to recognize when it's the end of the road, to pivot. I mean, I think that that is incredibly powerful. I think, you know, so many people get stuck and aren't able to let go, aren't able to

surrender something, aren't able to get into acceptance. To me, those are incredibly powerful skills. It's powerful. That's not to say it's pleasant. It's unpleasant, that's how. When you don't get your way, when you have to walk away from something that you've become That's not to say it's pleasant. It's unpleasant, that's how. When you don't get your way. When you have to walk away from something

that you've become so identified with. You have your favorite church old quote in the book, The One About Going From Failure, to Failure, you know, I'm sort of unbroken. But I also love his famous quote about, you know, never, ever, ever, ever, ever, ever give in. And then it gives the two conditions under which you absolutely should give in. Yeah.

Yeah. He's, he's, uh, he's got a lot of great quotes. Yes. Well, well, but we don't, we don't like that. We, we like the idea of you never, ever quit. Um, but if you never quit, I mean, that's how you die. You know what I mean? Like that's how you get yourself in serious trouble. Or you just end up throwing yourself against a wall or you, you pointlessly play a losing

hand. Or you end up getting assaulted by the mob and arrested by 17 FDI age. I'm not sure I can stand behind. You never, ever, ever quit anymore after that experience. Yeah, of course. Yeah. I mean, yeah, what if you're doing the wrong thing, right? Or what if it's the wrong thing for you, or what if it's the wrong time? I mean, there's a bunch of reasons. That's not to say, again, you quit entirely, you quit working at all, or even that you have to quit that thing, but the idea that timing doesn't matter, all these factors matter about when you should do something or continue doing something. Absolutely. I mean, what I learned, I learned so many things, but one of the things that, one of the safety guards I have now in place is I have what I call like my panel of people who I really believe in in their rationality.

I believe in their ability to think things through. I believe that they're not fear-based people, but they're rational people. And so when I have these great ideas, or I'm feeling like maybe I'm a little over my head here, I'd bring it to the panel. Because I, on my own, will chase it into hell. Yeah, you're bored of advisors. I have that group too,

where mostly what I want from them, it's like here's what I wanna do. Here's why I think it's a good idea. Here's why I think it's gonna work. It's like, look, a lot of people, it's like, I'm thinking of starting my own business and everyone's around them's like, no, you gotta get a job, you gotta do something.

Say, most people you have the people around you who convince you why you shouldn't Put yourself out there, but I think if you're entrepreneur driven or talented or you know elite and what you do You have the opposite problem and you have to cultivate the people around you that can you can go to and go Tell me why this is a really bad idea like tell me what I'm not checking Yeah Like tell me what I'm not. I'm checking. Yeah. Mm-hmm. Mm-hmm. Yeah. But you have to handselike those people very carefully, and sometimes you don't listen to them. But I think it's a great exercise.

Yes, for sure. No, I try, and one of the things I found with those people is I try to go, like, I want to make sure that I frame it in such a way that I'm not tipping my hand. Like, what do you think of this or like, or if I think it's a really good idea, I'll go to them explaining why I think it's a bad idea, like actually trying to make my own case. So they'll either be like, yeah, I think you're right.

Like thinking that they're telling me what I want to hear, but they're actually giving me, you know, the honest take on it. Because I think so often the reason we don't get that feedback is that people don't want to hurt our feelings. Yeah, and my panel doesn't care about hurting my feelings. I have people that are like, you know, there's very few people in life that will be super honest with you.

Yeah. And if you can find those people, I think you keep them and you don't discourage them from, because it's a gift, you know? Well, and understanding the incentives or the bias operating on the people around you, like I was just talking to my agent about something and my agent's great and we have a long-lady. I trust him, etc.

And but I have to be aware of the fact that you know this way involves a large commission for him and this way involves nothing for him. As a human being that is going to influence how he sees things. that is going to influence how he sees things. Of course. Yeah, you have to figure all that and make sure that the people that are sitting on your panel aren't going to be, for that one maybe he's off. Or you just get someone else's opinion to counterbalance that and if they agree great, if they don't, then there's something more you have to explore there. Right, right. No, and so if they were only financial biases,

it would be so much easier. The problem in life is that it's more often like, someone's identity is tied up in something, and so you're not even totally sure why they're reacting so strongly to this or that or steering you this way or that way. And you know, it has nothing to do with you and everything to do with something that happened to them 20 years ago or whatever.

Yeah, I mean, they're human psychology is endlessly fascinating and it is also sometimes a bit sneaky. That's very sneaky. Even to them, you know, because so much of what's going on is subconscious. Yeah, we like to think we're these super rational, super controlled people and we're the opposite of that. Opposite, super emotional. Yeah. Well, that's what I thought was so fascinating

about the games in the book, which is that like you have these super talented, super powerful, super well off people, and they kind of have this like secret addiction, basically. They're like totally powerless over this like habit or, you know, activity that they're hooked on. Most of them, yes. And I didn't recognize that in the beginning. Yeah. Because I came into it, you know, I basically was just going to take a year off and go to

LA because I wanted to be warm for a year. I had been chasing winter, my whole life. I mean, even during the summers, we go train places where there was snow. So before I had to law school, before I went into another very serious regimented life career, just wanted to be young and be a kid and be warm for a year. And so I ended up, you know, just being a cocktail atrus in the beginning for these games. And I was in my early 20s and from a small town. And I thought people that had made it to the places that these people had made it. Had it all under control. Yeah. You know, I thought their money was endless. I thought their self-control and their agency over them, self in the world was rock solid.

You know, you're just, you have these people in a pedestal and really quickly, it became apparent that that was not the truth. Is this thing all? Check one, two, one, two. Hey, y'all. I'm Kiki Palmer. Is this thing on? Check one, two, one, two. Hey y'all! I'm Kiki Palmer.

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No, I related to that in your stuff too, because I feel like my 20s were sort of similar in that like, you get good at something, there's something intoxicating and interesting and kind of like secretive about something. And you know, you just kind of get sucked up in it, and you don't question it because there's a large financial reason not to question it. And the fact that people don't approve or don't like it works against you because far from who you want to be, what's right, you know, what's the best use of your skills, talents, etc. Yeah.

You just basically summed up my 20s and everything. And in retrospect, it's like, you're like, who was that person? But it felt like it made sense at the time. It made all kinds of sense. And, you know, I think that I, I think I got to LA and I've never felt so small in my entire life. Yeah. You know, and all of a sudden here was this, because I started out, a cocto-atres and a waitress and a personal assistant for some really controlling people and all of a sudden I start you know waitressing at these games and then just have this crazy thought well maybe I can start my own games with these people and never

thinking it would work because everyone in Hollywood had a game, and those people were like running movie studios, and starring in movies, and worth a billion dollars, and yeah, I was like small-town kid. Anyway, I started these games, and my game became the go-to game, and it's like all of a sudden, I feel like I'm someone, you know? And I feel like I have, I feel like I'm power, you know, and I feel like I have I feel like I have power and I have

influence and that was the most addictive drug that I have ever been on Particularly the room where it happens. That's what we all want Yeah, to be in the room where it happens and then it could be different different things happening But like if you have a sense that you're at the center of something that is cool or important or whatever, it's very hard to question that thing. Yeah, especially growing up in the family I did

with my brothers doing what they were doing and their skill sets so clearly defined from early on and basically both kind of prodigies and all of a sudden like here I am and it's exciting every second, adrenaline and making so much money. I'm privy to these conversations, I'm in access to information, I've access to almost anyone and anything. And then, you know, like, just the stupid things, like, I'm dumping out a bag of a million dollars a calf in a hotel room and being 25 years old is like, it's intoxicating. It's intoxicating.

Yeah, you mentioned your dad, you mentioned your dad earlier. I've like both my sister and I clearly have something where we were both very attracted to sort of like powerful, complicated, insideery worlds. Right? Yeah. And I wonder what that is. Did you thought about what that was for you? Um, you know, I, my dad's larger than life.

Very charismatic. Um, I started out, I mean, I was a voracious reader of fiction. Loved fantasy and fiction and exploring new worlds and felt pretty bored in school. You know, I was a good student, but always had a taste for the sort of like fantasy worlds. Yeah. And then what about you? I think it's that. I think it's like it's a wanting, it's like if you feel like you need to earn someone being proud of you, or like you have to earn, being proud of you or like you have to earn being significant or mattering,

instead of just being entitled to those things as a person in the world and a family that loves you, right? It's not that it makes you vulnerable. I mean, it's propulsive in the sense that it makes you go out and do stuff. It's sad in that you'll never actually get that thing. And it can take you into some dark places to get there. Yeah, interesting. So, what's your sister do?

I don't want to get her in trouble, but she works for a very important, like not in trouble, but I don't wanna, anyway, she works for an important person. And it was just like, and I had worked for an important person when I was in my 20s. And they're very different people in very different worlds. But I remember my aunt was pointed out, I didn't even see it when she was like, you and her sister both ended up doing like the very similar things.

And so it was like, what do we have in common? Like, who is that person to us? And unfortunately, I think a lot of times, there's a lot of dad energy in those things that were like, the people were attracted to the work that we do, the attention we want. It's a sad fact that I think a lot of people are trying to earn, I'm proud of you, kiddo.

Yeah. Oh my God. Yeah. I mean, I can't tell you how many times when I speak, you know, and I'm on the speed and circuit, and people come up to me after. And all they want to talk about is the scene on the bench with my dad. Yeah. Because they're all relating to it. Yeah. Yeah.

It's so sad. There's that Philip Larkin poem. They fuck us up, mom and dad. I don't know about it. I don't look it up. It's so good. Here, let me pull it up. It's so good here. Let me pull it up. Okay. Okay. Uh, fuck us up. It's so good. Um, he said, uh, let me find it. It's, he said, they fuck you up your mum and dad. They may not mean to, but they do. They fill you with the faults they had and add some extra just for you. I'm going to put that in the nursery. Uh then he says, but they were fucked up in their turn by fools and old-style hats and

coats who have the time were sopmystern and half of each other's throats. Man hands on misery to man. It deepens like a coastal shelf. Get out as early as you can and don't have any kids yourself. Too late for us. Yeah. It's weirdy good, but. No, but I think you, when I think of the Mr. Roger stuff,

like you're special just by being you, I'm proud. I think what he was realizing is that if you try to make love, affection, you know, your place in the family, any of that stuff conditional, you are teaching, you're not just teaching your kids about this, but you're making them vulnerable in the sense that you are connecting, you know, who they are with stuff that's not in your control, right? Like, you know, you can get hurt and then you can't be the gold medalist that you wanted to be or, you know, your ideas could be ahead of their time.

So you're not seen as the genius inventor that your parents want. Yeah. Yeah. Success is a thing that it doesn't, it's not a guarantee. It's not if you do this, if you do X, you get Y, you know? And so it's, I think it's hard, it's, it's, it's hard if your identity is tied up on earning or achieving or getting certain stuff. Especially because even when you get there in my experience, it doesn't check that box. You know, that's not what checks the box.

Well, I imagine in your, what is that behind you that's moving? Is you have a cat back there? Is that your dog? Yeah. Yeah. We're blended in with the couch and I was like, I think your couch is moving. But I think you must have seen that in these rooms.

These are the people who, as far as America goes, the American dream is a movie star. You become a world famous movie star, sex symbol, millionaire, etc. That's that is the modern American dream for better or for worse. What percentage of those people were you like, I would trade places with that person. It seems fun to be them. Well, first of all, it was interesting because what I saw at the poker table is that there is a hierarchy. Okay. So and interestingly enough, the billionaires were at the were like sort of Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's Taker's the excitement was palpable. And the truth is is that I would not have traded places with any of them. I would have wanted their certain things that they had, but they were on that hedonic treadmill, and they couldn't get off. You know, it was just the never enough. Did you read the,

did you read the psychology of money? Yes, yes. Okay. I had him on the park. We're in Oregon. It's great. Yeah. Yeah, he's awesome. And there's that story in there that he tells that I just think is so significant of most of those people that I met and it's about Joseph Heller. Remember the story in the book? Yeah, enough. Yeah. It's in stillness, too.

It's in my book stillness. Yeah, it's never enough. Yeah. Well, yeah, the hierarchy, too, of like the writers at the House of the Billionaire, because the billionaire wants to be around famous people who've done different stuff. It's weird. My favorite thing in Morgan's book was the you're driving a Lamborghini. You think people are going look at that cool guy in the Lamborghini. I wish I had a Lamborghini and they're not thinking about

you at all. Love that. Yeah. Love that. Absolutely. It's. Or the other one of like, look at that guy. I know. You know, or the, what a douche. They're really trying to make us look at them. Yeah. Yeah. Yeah. It's weird.

I mean, it feels judgmental. You see these people and you go, oh, it's no fun having them. And there's probably a bit of envy and insecurity that just assumes every talented and successful person is deeply unhappy. But you do get the sense that the people who have it all, who got the thing that you think would be so transformative and amazing, it's always anti-claimactic and it never fixes

whatever the inside problem is that was motivating them to get that external thing in the first place. So one time Matt Damon played. And this is a really bad experiment. And so I'm just as he seemed like he was free from that. Yeah. He seemed like he enjoyed his life, but didn't need what a lot of the other ones needed. Like he seemed normal, if you will. Well, to me, that's the best.

And that could be totally wrong. But it could be a monster. Yeah. But no, to me, that's the much more impressive accomplishment, right? It's like, OK, so almost invariably, the person who is the absolute greatest of all time is there's something in them that they always have to one up and that's what gets

them there. And that's probably once they get there and there's no one else to one up, there's an emptiness there. You know, like it doesn't seem like it's fun to be Elon Musk or something like that, right? And but like to me, it's much more impressive when you meet someone who is super talented, super successful, has accomplished something that objectively, you're like very few people have ever done that. And you're like, I admire that person as a person, even so.

Character, yeah. Absolutely. And they have, you know, their humble and gracious and not petty. Yeah. You know? The torture genius thing seems like a shitty way to... That seems like a bad trade-off. If you're like, oh, to be great, you have to be a drug addict,

or you have to be an egomaniac, or you have to be a ruthless killer, you know, like, that seems not worth it, especially when, like, being 15% worse, but a 100% happier still is a pretty good deal. Yeah, for sure. And I mean, I also, I arrived at those places that I thought would grant me that I thought would grant me so much happiness. You know, I was on the private jets and I was vacationing on huge yachts and I had a lot of money in the bank and I remember like the third summer

that I went to the South of France on a big boat. I was like, this is fucking boring. You're like, this is boring and it's the same conversations and like kind of like having this realization, that's cool. You know, this means I can go back at some point to, and it wasn't for many years because I was caught up and I was addicted. But this idea that I could go back to the life

that I had growing up, which we were middle class, we weren't poor, and we had cool adventures, and went skiing, but we weren't Uber rich, and we didn't fly on private planes, and I had this really cool, adventurous life of substance. And it's a lot easier to achieve that than super yachts in the South of France, you know? Yeah, I mean, if like, being rich to you is having the most money in the world, that's a one, it's a moving target.

And it's a, you have to do a lot to make that much. If, you know, if like being rich to you is like middle class, right? Or if your needs are X, we are like, my definition middle class is like the middle, like that's a very large target. That's millions and millions of people have done, right? Like, so I think, I think it comes down to sort of what are you attaching your identity That's a very large target. That's millions and millions of people have done, right? Right.

So I think it comes down to sort of what are you attaching your identity or what your definition of success is? I was talking to this football coach once, and he was telling me he was like, he would pull up. Every year he was like sports illustrator at ESPN would publish the 10 highest page coaches. And he was like, if I was not on that list, I felt like not good. And I would call

on the LMI agent, right? And it's like, like the 11th paying coaches still making literally millions of dollars, playing a, you know, coaching a game for a living in front of it's still pretty great to be 11, 12, 13, 14. Like, so if you. So if you can have a different definition of success, it's much more attainable, much easier. And then also, you're less paranoid because you're not in this kind of zero sum, like if one person gets ahead of me, it all falls apart mentality. Yeah, that's stressful. Yeah.

That's super. That's hectic. Like, it's really, I'm looking for purpose, financial independence and contentment. Yeah. Right. You know, but you can be very rich and not be financially independent, right? Because of, you decide what your needs are. Yeah. And your soul's kind of for sale of it determines you decide what your needs are. Yeah, and your soul's kind of for sale of it.

You have to make decisions that aren't aligned with the truth of who you are or, like the principled life that you wanna live. I mean, that was a huge thing for me is for the first part of running those games, I was really able to draw that line in the sand about who I was morally and not fear too far from it, you know. And then when I got to New York and the game started, I started running these humongous games. People were winning and losing $100 million a night. I was at, you know, my head got messed up. And

I started making choices that were not aligned with who I was inside. And I would put people in, in games that perhaps couldn't afford it. People I knew for sure were gambling addicts and slowly inch by inch, I became this person that I couldn't stand. And then go ahead. No, I mean, and then it was like the dominoes fell. Yeah, I got out obviously before I got arrested, but looking back on your story,

if someone is sort of they woke up and they're like, how did I get here? This is not who I want to be. This is past some sort of, you know, what I'm okay with, not okay with, or I have some premonition that it's, that this is spinning out of control. What do you feel like you've,

having gone too far, what do you feel like you would say to a person in that position? Someone who has kind of identified that they have, they've drifted from who they know they should be or what they're comfortable with because it's lucrative or exciting or anything. Yeah well it's really hard to back off that. But it's also really really empowering and so I think you know sitting down and doing some real deep investigation. doing some real deep investigation, some writing.

Who did I wanna be when I was a kid? Yeah. You know, who do I wanna be now? What do I want my legacy to be? What do I think my limitations are if I continue to make these immoral choices? Is there a way to get both of the things that I want? You know, widening mean what you think is possible in the world. Because we get real caught up in the narrowness of our path and we stop to see that there's

multiple paths. Sure. It could branch up at any time and go in a totally different direction. And I just think moral courage. I just don't think there's many things cooler or more majestic than moral courage. And it's such a rarity. What's very hard to say no to money? Very. I'm really good at it now. What have you learned?

How do you get good at that? Well, you just lose everything. You move into your parents' basement and you have to get good. Get face to face with being totally broke at 35, living in your mom's basement and then you, no. I mean, hopefully that's not what it takes, but that is what it took for me.

And not just that. I mean, there is a whole path that involved a 12-step program for an amount of time and this incredibly wise woman that I met there who told me that I could be a woman of dignity and honor again and like what that felt like and this very noble criminal attorney who said integrity is going to be how we proceed and just you know surrounding myself with these people

um both accidental and intentionally that spoke to that that higher part of me and and and that higher part of me and helped me remember that, like, that is who I want to be. And that is, you know, when I was little, I had a huge conscience and I wanted more than anything to make positive impact in the world and to be a good person and to be this like spiritual warrior. You know, I mean, those were the things that I wanted to be. And then I became this person that was obsessed with money and that like, spoken this weird way. And it was always like, hot-slinging and making deals. And that was also cool and interesting. But, you know, and I like, I love that I have that skill set.

But I needed to come back to being able to believe in who I was, who I am as a human being. I do feel like if it's rare enough, you could define it as a superpower. And the ability to say, like, if someone offers you a large amount of money to do something that you shouldn't do or do something that you just actually aren't that excited about doing. Yeah. To be able to say no to that is like the rarest thing in the world.

I struggle with it so much. It's so hard. Yeah. Even if you know, even if it's just like, yeah, it just feels, it just feels, there's something about it, especially also, if you have identified, to go back to what we're talking about, if there's something about making someone proud of you or proving your worth or if you've defined yourself

by those things, you're like, it feels like almost like a little bit of death or something to be like, no, I'm not gonna do that. Major FOMO and fear. Yeah. Maybe I won't get this opportunity again. Sure. But I mean, you know, when the prosecutors wanted me to, because this was a Southern District,

and there were so many politicians and billionaires and celebrities and people of note that played in these games and the prosecutors assumed pretty accurately that I would have this inside information that would lead them into other and listen, you know, if there was a Weinstein or an Epstein in my game, I would have come to that, like, I would have given them whatever, but these were people that were like vetting sports, which is now completely legal and you can just open an app and everything's a betterable moment, you know, but when they when the deal was that they would keep me out of jail and give me all my money back if I become a confidential informant and I passed on that, informant and I passed on that. There is this feeling of holy shit. I am a pat like this is power. Sure. You know, this is this is what I have been searching for ever since I was a little girl feeling powerless. It's not the look at how much money I have in my bank account because

then if that goes away You're not powerful anymore. This is it isn't like look at my friends look at who I roll with It's like having this inner power of I know who I am I'm gonna be okay and I am and there's nothing in no one that's gonna, that's gonna get me to do something that I don't fundamentally believe in. Yeah, I think you say in the book that was like a $5 million decision, right? Something like that.

At least. Not a lot of people can, I mean, if you think about it, it makes logical sense why that would be empowering, right? Because it's like, how many people are so rich that they could give up $5 billion, right? Like not very many people, right? And so even though you couldn't really afford

to give up $5 billion, you had gotten to a place sort of spiritually and ethically where you could and so You know, it's like if you smile you feel happy if you Be like what's five million dollars to my reputation? Right that you're a very wealthy person right even if you don't have any money and I didn't want to be owned by Right, You know, that's interesting.

Yeah, I've been thinking about that recently, like just, yeah, and now that I have, you know, the ability to sort of do whatever I want, when I, you know, people will ask me to do stuff, I'll be like, I don't agree with that. So no, or I, I don't like your clients and no, or what it was. Anyways, it's something I, I something I would probably have said yes to in a thirstier place in my career. Yeah. Yeah.

But what's interesting about it is how, to go to your point, when you do it, by practicing that thing, you become that person. So by saying no to it, I don't like that. I'm not interested. Or, yeah, you're offering me to do this, but that means I have to skip my kids first day of school or whatever.

When you say no to that, it's not just the effect of simply having done it, but having done it, it changes who you are and how you see yourself. And it's this kind of reinforcing mechanism that's really empowering. Absolutely. Absolutely. And I mean that's how you change that is how you become something or someone. Yeah, by acting as if. That's right. So your view is sort of virtue, integrity, ethics. This isn't just this like conscience you have. It's, or this thing you're born with,

it's a thing you do. We're don't do. I think it's, well, I think that what I realized is yes, I was, who knows if I was born with it. My mom, whereas my dad stood on this soap box of constructive suffering and discipline and accomplishment, my mom was equally passionate about be a good person, have integrity, be kind. Let's look at how you showed up in the world. And so I was socialized in this way.

And then I veered from it. And I hated the way that I felt about myself and the world. And so a return to it was really necessary. But what I realized is that character, good character is not a given, it's not easy. It's something that needs to be worked on and trained. The world will try to derail your character, survival, you sort of get this idea that in order to survive, you have to compromise your character. And so, something I learned, and then it was further underscored when I was doing a 12-step program

is this is something that you work on, you train in. And it's a buildable skill and we should not assume that it just either is or is not. Yeah, it's, someone said something once there was like, love doesn't exist. There are only loving actions. And maybe that's the same, you know what I mean? Like having a conscience is great. Knowing right and wrong is great. But really, it matters what you do. And the more you do that thing, the more you become that thing.

Yeah. you do that thing the more you become that thing. Yeah, so at the end of the day I look at a short list of what's important to me and I look at how I did and I know what I have to work on and hopefully I work on it. Yeah, my favorite 12-step thing is it works if you work it. Yeah. You know, it's like, if you do it, it tends to work for you, but if you don't, it doesn't. It's so true, and I have to say, you know, for five years, I was part of that world and the people that came into those rooms No matter how destroyed their life was if they did this stuff It worked yeah And I think I've thought about it so much because there's

The whole world is a self-help cult now, you know But and and so much of it isn't effective. And I think because self-help doesn't take into account what it means to be a human being. I think people change within a paradise, like within a community because there's all these social rewards and everything. So doing it within a community, a culture, within a community where there's accountability and then there's social status. If you do what you're supposed to do, that is such an effective way to change behavior. Whereas when you're just trying to do it by yourself, it's so hard. Well, I'm sure you experienced this.

Like anyone who did one thing for a while and now does a very different thing and, you know, reflects back or is identified for having, you know, turned on something or, you know, turned their life around or whatever, people always go, well, when was the moment that you knew, right? Because they think that transformation or change is the result of some epiphany. Like, I went through this the other day, I went back and I read one of my favorite books, which you would actually really like. I think it's called The Harder They Fall by Bud Schuylberg.

It's about this PR guy in the boxing world in the 50s, and it's about this sort of, he's gets sucked into this sort of mob underworld, you might relate. Anyways, it's a really interesting book, but, um, I read it, uh, when I was in marketing and, and in my mind, looking back, that was the book that shifted me leaving American apparel and changing my life doing all this stuff. And so I reread the book like a year ago or something. And I found like exactly like I'd highlighted this page where I would it was like, you know, you cannot deal and fill without becoming the thing you touch. This beautiful passage, right? And I was like, this is

this is it, right? Even rereading. I was like, this is obviously what changed my life. And then I was like, when did I buy this book? So I pulled up Amazon and I found like when I bought it. And it was three years before I left. So I went to work almost every day for three fucking years, having had the epiphany before any change actually happened. So, you know, it's never this overnight instantaneous thing that we want to think that it is. It's about systems and communities and all the stuff we're talking about. And breaking and whatever your current circumstance breaking you down, breaking you down, breaking you down until you get desperate. And another thing that they talk about in the program is like the gift of desperation. Yeah. Yeah. Your parents basement being that I imagine. Yeah. There's a lot of gifts. There's a lot of gifts of desperation, if you will.

Yeah. Yeah. Yeah. And if you can get out without hitting rock bottom, as they say, kind of yourself very, very lucky, because you're the exception not the rule. Oh yeah, well I had a couple of rock bottoms. Yeah no it's one piece of advice I got. I be curious what you think because we're talking about the sort of worlds and changing etc. I forget to set it but they said just because you're good at something doesn't mean you have to do it for the rest of your life. Oh, I love that. For sure. And, you know, I think a lot what we're talking about here, passing on money, picking, choosing virtues, just because you're good at something. It's all kind of, you know, what it is, it's like time is the most limited resource we have. How do you want to spend your time?

Right, right. You know, that became super compelling to me after I left that world because there were years where it was really fun. I'm not going to lie. It was a really, it was like a video game. Like, I was, you know, like every second you you had to figure out, this person was trying to take your game and this person was trying to stiff you and you're driving around and you're Bentley

and you're an idiot at 23 and like, it was fun, you know? But then it got not fun at all. And I had to like, deal with people almost exclusively that I did not like. Yeah. And I spent all this time doing things I did not want to do for money. And when that was done, you know, there was a grief period, but then there was like, oh my God, like, you know, I live with my mom, but like, I don't have to talk to that

dude bag anymore ever again. I don't have to try to collect money from, you know, people who have more money than God in their, are playing these games with me. You know, I mean, there is this moment where I was like, I'm not going to spend any more of my time doing something that I hate. Yeah. Yeah. Well, and it's like if you spend a lot of time doing things you don't like for people you don't like, even if you are very well paid, you're not very rich, right? No.

You don't, you, you're rich. You have a large bank account, but you're not in rich, right? Like, you're rich, you have a large bank account, but you're not in control of your life. This is what I was saying earlier, it's like, you can be very rich and not have financial freedom, and you can be pretty poor, you know, and be quite wealthy and have a lot of financial freedom. Yeah. Yeah. It's just a matter of,

well, I think it comes down to sort of What are your needs? What's what what's your hierarchical? What are your hierarchical needs people are making differently? There's not a one-size-fits-all I think there are some people who love love love love love love money and For them to pass on it and have more time would be a terrible idea for them. Because they fundamentally love making money and love being rich. And I like money a lot.

I like nice things. Don't get me wrong, you know. But it's not the first thing. It's no longer number one line for me. So I think it's like really figuring out who you are, what makes you tick, and then sort of systematically, you know, taking out the things that you're afraid to take out, but you don't work for your life anymore.

Yeah. So much of it is fear, and walking through those fears is so important. Well, and look, like making money or being famous or whatever is a byproduct of you doing what you like to do when you like to do it, that it's great, right? The problem is if you are doing things you don't like to do, if you're not in control of your life, to get this thing that you've lied to yourself by saying that when I get it, I will be happy, free, you know, ethical, etc. It never happens. The goalpost moves.

Yeah. I mean, and you know when I realized that more than anything. So I burned it down. My life was destroyed. I was 35 years old, millions, millions of dollars in debt, convicted felon, social pariah. The tabloids were telling me this awful stale. I had very few friends. I had no money, not a bank account. Like, you know, I was addicted to drugs and apple. I mean, it was dark days, okay. And I figured out a way and clawed my way back at Goksober. I wrote a book and I did it in a way that I still could feel proud of because of course the publishers

wanted this big celebrity takedown piece, which I didn't write and then, you know, I published the book waiting for my life to change. And that didn't work. But when I had gotten really clear on the solution, I felt like the most usable, monetizable asset was the story. And so I wrote the book, book didn't work, didn't sell, did not change my life. And then I was like, okay, it's going to have to be a movie. And then I started going to Hollywood and getting all these meetings with these really important people. And then everyone would call

and say like, we're passing. And I'm like, you know, I feel like I'm a pretty good read of people, but So some things some things amiss here. So then I got really brave one day And I asked this exact at one of the big cable networks. I was like, okay, but why are you passing? Yeah And he was like Malia I got a phone call You know, he's like there's a lot of really powerful people You know, he's like, there's a lot of really powerful people that are, and I was like, why didn't I think about that? You know, I was just like in this, like, that's so obvious.

And then, so then I went home and strategy, like, has always been something that's not only very fun for me, something that I have apt to for. So I was like, okay, on all these meetings, what did I learn? I learned that there is a short list of people in Hollywood who are gods who don't have to play politics, who when they make a move, everyone goes, okay. And so I made that short list and it's like Sean DeRyme's Tyler Perry, Steven Spielberg, Aaron Zorkin, and Aaron Zorkin is my favorite writer. And I was like, why not, why not just try to get a meeting with him?

If he is the type of person that he writes his characters to be, he's not going to let some rich person write. So I got the meeting with Aaron, and it was really hard to get the meeting with Aaron. And so I flew to LA and I told him my story and he said something hilarious because he's there and he was like, well I'll tell you one thing kid, I've never met someone so down on their luck and so full of themselves. I was like, well I'm doing a good job of faking it because I'm not full of myself right now. But what I was was I had lost everything.

So ego was gone. I was fearless, you know, because I had lost everything. And so and failed so spectacularly. And was such a loser by my society standards, you know. And so he decided to write the movie. And and so I'm like like the movie's about to come out. I know it's good. It's written by Aaron Sorkin, who is the highest paid screenwriter in the world. And the studio sends me a big bank wire because I had negotiated my ass off for that life rights option. And so I have money again. I'm about to, you know, sort of have this movie about me

and I waited for that feeling of okness to come. And it didn't come. It did not happen. And so that's when I knew there's something else to it here. And I have to figure out what that is because I can't keep chasing these things and get to the top of this mountain and realize, it's not real. It don't get me wrong, that movie changed my life. It saved my life. It gave me incredible opportunities.

I had deep and still do every day deep gratitude, but it was not the answer to this existential question that we're talking about of like, how does a human being find happiness, contentment? How do you feel, complete? How do you find peace? Beautifully said, I think that's the perfect place to close. Okay.

Awesome. Awesome. Yeah. Awesome. Hey, it's Ryan. Thank you for listening to the Daily Stoic podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in a couple years. We've been doing it. It's an honor. Please spread the word, tell people about it, and this isn't to sell

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